Social Question

What is the most awkward attempt that you have had at flirting?

For me, it was when I was talking to this guy named Max – I was trying to say that it would be really cool if his full name was Maximillian but for some reason I said “It would be really cool if your name was Maxi-pad.”

21 Answers

“Sooooo…...............................................Wanna make out?”
“Uhm, no”
“Ok….”
Extremely long, awkward silence. Then I walked away. It was at some high school party. I have definitely learned a lot more about talking to women since then lol.

I’m always totally oblivious when cute guys flirt with me. At a restaurant in Italy the waiter brought my friends and I our fries. He set a plate down in from of her and said, “your French fries.” and held my plate away and asked me,” baked potatoes? Mashed potatoes?” and winked. And I was like, “what? No. I got fries.” and he just set them down and walked away. My friend said, “wow, real smooth, he was flirting.”

@troubleinharlem It’s painful to try to make small talk when you’re very nervous. Sometimes I think it’s better to break the ice as soon as possible than to do the whole, “So…...what kind of…..dog, do you have?” Lol.

My incident took place at the Mellow Mushroom pizzeria. I was out with a bunch of friends and I was already drunk. I happened to be hanging out with my really hot bisexual friend who we will call Liz. Liz and I happen to have the same taste in women, so it often gets competitive between us. Luckily, we are both about the same level of awkwardness, usually.

Anyway, we were eating and our waitress was incredibly hot. She carded me and said “1990, huh? I’m a 90’s kid too, but I was born in ‘91.”

“Yeah, uhhh, well I wouldn’t have guessed that because you… uhh… look older and stuff… because you’re pretty,” was my response. She smiled and walked away.

Later, Liz looked our waitress dead in the eye and said “you’re really hot.” Again, she smiled and walked away.

By the end of our meal, Liz had written my name and number down on a napkin and left it under my cash tip. She did the same thing with her own number. We hightailed it out of there after that.

Two days later, Liz texted me and asked if I got any phone calls or texts. I said no.

At the conference center where I worked for a few summers, I had a crush on one of the older staff members. He handled my flirtations beautifully. One day, he said, “You remind me of my sister. From now on, I’m going to refer to you as ‘Little Sis’.” And he did. It kindly let me know where I stood.

@Judi The same here. It was the charming piano player in the restaurant where I used to hang out.

One time this attractive neighbor came over and she looked quite fetching.

I meant to tell her that she looked “out of this world”, which in those days was considered to be a very flattering compliment, the implication being that the person looks so much better than anyone else on the planet, that their appearance is “out of this world”.

However, instead of that, I told her that she looked like she was from another world. ;-p

so I wrote my number on a napkin for this really cute waitor at a restaurant, (and winked of course), after flirting a little back an forth. He seemed intrested enough. While I was leaving, I saw his boyfriend come over and kiss him. Oops. I guess my Gay-o-meter isn’t working to great.

I had to think back, digging through flirting ‘cobwebs.’ The most awkward was when I was about 12—I was in this phase where I really loved baggy flannel shirts, ripped up jeans, real Native American moccasins and a baseball cap. I went to the mall one day with one of my friends and she went into a store like Claire’s- I didn’t feel “foofoo” that day so I sat on one of the benches slumped over with my forearms on my knees, peering from under my hat while people watching.
A group of girls walked by, stopped, wiggled their fingers and giggled, whispering and looking at me, giggling more. I was completely puzzled and just ignored them. That just made them giggle more until one girl stepped forward like she was going to talk to me but my friend (very girly-girl) came out of the store. They stopped, looked at each other and the group left.
It took me about…. 5 or 6 hours to realize exactly what had happened.

Most attempts to flirt were awkward for me. I gave this a lot of chances and wanted to improve but it never happened. So i stopped flirting and only enjoyed the company of other womens till I stopped being single. Then flirting seemed to work out better but I didn’t do it because I didn’t want to be rude.

One day, I was at a restaurant with my friends. The waiter we had was very cute and I was flirting with him the whole time. When it came time to leave, the waiter invited one of my guy friends home with him and proceeded to call me a freak. It was strange.

I’m not sure if this counts, but it is the only embarrassing flirting situation that I can think of right now. I was standing in my driveway with a guy friend, when I got the vibe that he was going to try to kiss me. I was right. He leaned in, and I panicked, and like an absolute jerk, I instinctively spun around and turned my back to him. It was awful. I feel bad to this day, although he has since passed away. I think about that night every now and then and I just cringe.

In college I noticed a girl in class I thought was attractive, and decided on the way out I would strike up a conversation. So when class let out I attempt to exit the same time she is but one person got in between us and then as we hit the hall two people were between us. Thinking I could correct the situation I started moving a little faster to get around to her, but just the way the crowd moved more and more distance got between us. While I was getting increasingly aggressive to get around the crowd I realized I was on her radar and she started moving faster to get away from me as I was looking like a stalker at that point. Looking foolish but being committed I kept pushing through the crowd and blew right past her to make it look like I was late to get somewhere and it wasn’t really about her, which of course it was. Awkward!!!!